Chloride → 1-Benzylpiperidine

HRID 846592Notes

Reaction equation

HRID 846592 reaction equation
[Cl-].[CH2:2]1[CH2:12][CH2:11][N:10]2[C:5](=N[CH2:7][CH2:8][CH2:9]2)[CH2:4][CH2:3]1.[C:13]1(C)[C:14](C)=CC=C[CH:18]=1>>[CH2:11]([N:10]1[CH2:9][CH2:8][CH2:7][CH2:4][CH2:5]1)[C:12]1[CH:2]=[CH:3][CH:14]=[CH:13][CH:18]=1

Participants

4

Reactant 3

HCID 312ChlorideHCID 7237O-XyleneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

Product 1

HCID 761901-BenzylpiperidineYield 60%

Conditions

Temperature
100 °C

Procedure

Chloride 12 (23.0 g, 1.0 equiv) was combined with DBU (20.4 g, 2 equiv) in 400 mL xylene and stirred at 100° C. until TLC examination indicated complete reaction (ca. 5 h). The reaction was concentrated to dryness in vacuo. The residue was dissolved in methylene chloride and extracted with water (1×). The organic solvent was removed in vacuo and the residue was flash chromatographed in 10% ethyl acetate/methylene chloride to afford 11.8 g (60%) of 11 as an oil.

Workup

  1. customreaction (ca. 5 h)
  2. concentrationThe reaction was concentrated to dryness in vacuo
  3. dissolutionThe residue was dissolved in methylene chloride
  4. extractionextracted with water (1×)
  5. customThe organic solvent was removed in vacuo
  6. customchromatographed in 10% ethyl acetate/methylene chloride

Sources & evidence

ORD record
ord-b32a4e342c9746cba75d45d4618eb696
Source dataset
uspto-grants-1992_08
Patent number
US05137894

Reaction notes

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